Why AI helps—but needs skillful guidance

In this episode of Distributed, host Jack Hannah sits down with Andrew Stellman, a longtime software engineer, author, and engineering leader who has written multiple widely used software engineering books published by O’Reilly.

Andrew reflects on how being forced into remote work after September 11th shaped his thinking about teamwork, what high-performing teams get right about alignment and mission, and why listening carefully is still central to building useful software. The conversation then turns to AI, where Andrew talks about why these tools work best when engineers slow down, think critically, and stay engaged with the code they are creating.

Andrew also shares five habits that help developers use AI more effectively, why learning to skim and read code matters, and why many of the challenges teams face today are not new, even if the tools are.

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Where to find Andrew Stellman:

• X: https://x.com/AndrewStellman 

• LinkedIn: https://www.linkedin.com/in/andrewstellman 

• Linktree: https://linktr.ee/andrewstellman

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Where to find Jack Hannah:  

• LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠⁠⁠⁠

• Website: ⁠⁠⁠⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠⁠⁠⁠

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Timestamps:

(00:00) Intro

(01:27) Andrew’s first experience working remotely 

(03:57) Why remote work depends on shared understanding

(06:54) Why trust is so hard on teams

(08:50) What high-performing teams have in common 

(12:03) Turning user needs into buildable requirements

(15:34) How to get better at explaining problems

(16:38) Why Andrew believes AI improves software

(19:42) Why prompt engineering is really requirements engineering

(24:20) How LLMs make shared understanding cheaper

(26:49) Why skimming is a critical AI-era skill

(30:05) Five habits for getting more out of AI

(35:40) A real example of the rehash loop

(37:59) Why software’s hardest problems haven’t changed

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Referenced:

• Jennifer Greene on LinkedIn: https://www.linkedin.com/in/jennifergreene

• Applied Software Project Management: https://www.amazon.com/Applied-Software-Project-Management-Stellman/dp/0596009488

• Learning Agile: Understanding Scrum, XP, Lean, and Kanban: https://www.amazon.com/Learning-Agile-Understanding-Scrum-Kanban/dp/1449331920

• Beautiful Teams: Inspiring and Cautionary Tales from Veteran Team Leaders: https://www.amazon.com/Beautiful-Teams-Inspiring-Cautionary-Veteran/dp/0596518021

• Head First C#: A Learner's Guide to Real-World Programming with C# and .NET: https://www.amazon.com/Head-First-Learners-Real-World-Programming/dp/1098141784

• On Writing: A Memoir Of The Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375

• Save The Cat! The Last Book on Screenwriting You'll Ever Need: https://www.amazon.com/Save-Last-Book-Screenwriting-Youll/dp/1932907009

• Why Projects Fail: https://www.stellman-greene.com/Why_Projects_Fail.pdf

• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• Beyond Vibe Coding: From Coder to AI-Era Developer: https://www.amazon.com/Beyond-Vibe-Coding-AI-Era-Developer/dp/B0F6S5425Y

• The Cognitive Shortcut Paradox: https://www.oreilly.com/radar/the-cognitive-shortcut-paradox 

• The Sens-AI Framework: Teaching Developers to Think with AI: https://www.oreilly.com/radar/the-sens-ai-framework/